Dimethylformamide → HCID 66603388, compound

HRID 1808769Notes

Reaction equation

HRID 1808769 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1.CN(C)C=O.[Cl:22]CCl.C(Cl)(=O)C(Cl)=O>>[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][C:10]([O:12][Cl:22])=[O:11])[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 132517844-(2-Oxo-2,3-dihydro-1H-benzimidazol-1-yl)butanoic acid

Product 1

HCID 66603388HCID 66603388, compound

Procedure

4-(2-Oxo-2,3-dihydrobenzimidazol-1-yl)butyric acid (50 g; 0.227 mol), N,N-dimethylformamide (1.84 g; 0.025 mol; 0.11 eq), and dichloromethane (480 g; 5,652 mol; 24.89 eq) were charged to a stirred-tank reactor. Oxalyl chloride (31.12 g; 0.245 mol; 1.08 eq) was then dosed at 10-20° C. over a 1-hour period while stirring. The resulting mixture was then stirred at 10-20° C. for an additional hour. All the above steps were conducted under a N2 atmosphere.

Workup

  1. stirringThe resulting mixture was then stirred at 10-20° C. for an additional hour

Sources & evidence

ORD record
ord-74d031bf1adc40bca21d4168b806b2dc
Source dataset
uspto-grants-2013_01
Patent number
US08362006B2

Reaction notes

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